BORON-CONTAINING HETEROCYCLIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Description

[0001] The present invention relates to boron-containing heterocyclic compounds for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these heterocyclic compounds.

[0002] In organic electroluminescent devices, phosphorescent organometallic complexes or fluorescent compounds are often used as emitting materials. In general, there is still room for improvement in electroluminescent devices.

[0003] Polycyclic compounds that can be used in organic electroluminescent devices are known from US Pat. No. 6,322,908 and WO 03 / 001569 A2. Compounds according to the present invention are not disclosed.

[0004] MUKUNDAM VANGA ET AL: "BN coordinated triaryl pyrazole: effect of dimerization, and optical and NLO properties", JOURNAL OF MATERIALS CHEMISTRY C, Vol. 7, No. 40, October 17, 2019 (2019-10-17), pages 12725-12737, , DOI: 10.1039 / C9TC04309H, first published October 19, 2019 (day.month.year) discloses compound B1, which remotely resembles formula (I) of the present application.

[0005] In general, there is still room for improvement in these nitrogen-containing heterocyclic compounds, for example for use as emitters, especially as fluorescent emitters, particularly with regard to lifetime, color purity, but also with regard to efficiency and operating voltage of the device.

[0006] The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which, when used in this device, lead to authentic device properties, as well as to provide the corresponding electronic device.

[0007] In particular, it is the object of the present invention to provide connections that result in a long service life, good efficiency and low operating voltage.

[0008] Furthermore, the compounds should have excellent processability, with the compounds particularly showing good solubility.

[0009] A further object of the present invention can be seen in providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, particularly as emitters. In particular, it is an object of the present invention to provide emitters suitable for red, green, or blue electroluminescent devices.

[0010] Furthermore, the compounds should lead to devices with excellent color purity, particularly when used as emitters in organic electroluminescent devices.

[0011] A further object of the present invention can be seen in providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. In particular, it is an object of the present invention to provide matrix materials suitable for red, yellow, and blue phosphorescent electroluminescent devices.

[0012] Furthermore, the compounds should lead to devices with excellent color purity, especially when used as matrix materials or as electron transport materials in organic electroluminescent devices.

[0013] Another task can be seen in providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality

[0014] Furthermore, the electronic devices should be able to be used or adapted for a variety of purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0015] Surprisingly, it has been found that certain compounds, described in more detail below, achieve this objective, are highly suitable for use in electroluminescent devices, and lead to organic electroluminescent devices that exhibit very good properties, particularly with regard to lifetime, color purity, efficiency, and operating voltage. These compounds, as well as electronic devices, in particular organic electroluminescent devices, containing such compounds, are therefore the subject of the present invention.

[0016] The present invention relates to a compound comprising at least one structure of formula (I), preferably a compound according to formula (I), where the symbols used are: Z a< , Z b< is, identically or differently on each occurrence, N, CR or the groups Z a< , Z b< form a ring Ar a< , where the ring Ar a< is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals Ar or R a<, where the ring Ar a< together with the CO group and the groups W a< , W b< forms a 5-membered ring; W a< , W b< is, identically or differently on each occurrence, NR, NAr, NB(R) 2 or NB(Ar) 2 , where exactly one of the groups W a< , W b< is NB(R) 2 , NB(Ar) 2 and exactly one of the groups W a< , W b< is NR, NAr, or the groups W a< , W b< form a ring of the formula where Z c< is R or Ar, the ring Ar b< is, on each occurrence, the same or different, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals Ar or R b<, where the ring Ar b< can form a ring system with a group R, Ar or Z c< or the rings Ar a< and Ar b< together can form a ring system, and the dashed lines represent the bonds to the CO group or group Z b<; Ar is, on each occurrence, the same or different, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R, where the group Ar can form a ring system with at least one group Ar, R, R a< , R b< or one further group; R, R a< , R b< is, identically or differently at each occurrence, H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar') 2 , N(R 1< ) 2 , C(=O)N(Ar') 2 , C(=O)N(R') 2 , C(Ar') 3 , C(R 1< ) 3 ,Si(Ar') 3 , Si(R 1< ) 3 , B(Ar') 2 , B(R 1< ) 2 , C(=O)Ar', C(=O)R 1< , P(=O)(Ar') 2 , P(=O)(R 1< ) 2 , P(Ar') 2 , P(R 1< ) 2 , S(=O)Ar', S(=O)R 1< , S(=O) 2 Ar', S(=O) 2 R 1< , OSO 2 Ar', OSO 2 R 1< , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or Thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups may be replaced by R 1< C=CR 1< , C≡C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , -C(=O)O-, -C(=O)NR 1< -, NR 1< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<,or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; or heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<; two radicals R, R a<, R b< can also form a ring system with one another or with another group; Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, where two radicals Ar', which are attached to the same C atom,Si atom, N atom, P atom or B atom, also by a single bond or a bridge selected from B(R 1< ), C(R 1< ) 2 , Si(R 1< ) 2 , C=O, C=NR 1< , C=C(R 1< ) 2 , O, S, S=O, SO 2 , N(R 1< ), P(R 1< ) and P(=O)R 1< ; R 1< is, identically or differently at each occurrence, H, D, F, Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2< ) 2 , C(=O)Ar", C(=O)R 2< , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B(R 2< ) 2 , C(Ar") 3 , C(R 2< ) 3 , Si(Ar") 3 , Si(R 2< ) 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which may be substituted by one or more R 2< may be substituted, where one or more non-adjacent CH 2 groups are substituted by - R 2< C=CR 2< -, -C=C-, Si(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , -C(=O)O-, -C(=O)NR 2< -, NR 2< , P(=O)(R 2< ), -O-, -S-,SO or SO 2 can be replaced and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or a combination of these systems; two or more, preferably adjacent radicals R 1< can form a ring system with one another, one or more radicals R 1< can form a ring system with another part of the compound; Ar"is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms,which may be substituted by one or more radicals R 2<, in which case two radicals Ar" which are bonded to the same C atom, Si atom, N atom, P atom or B atom may also be bridged to one another by a single bond or a bridge selected from B(R 2< ), C(R 2< ) 2 , Si(R 2< ) 2 , C=O, C=NR 2< , C=C(R 2< ) 2 , O, S, S=O, SO 2 , N(R 2< ), P(R 2< ) and P(=O)R 2< ; R 2< is, at each occurrence, identically or differently selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, two or more, preferably adjacent, substituents R 2< may form a ring system with each other.

[0017] Structures / compounds according to formula (I) are preferred which have a group Ar b<, where the groups W a< , W b< particularly preferably form a ring of the formula where Ar b< and Z c< have the meaning given above, where Z c< is preferably Ar.

[0018] The ring Ar b<, identically or differently at each occurrence, represents an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 50 aromatic ring atoms, which may be substituted by one or more radicals Ar or R b<, where the ring Ar b< may form a ring system with a group R, Ar or Z c<, or the rings Ar a< and Ar b< together may form a ring system, and the dashed lines represent the bonds to the CO group or group Z b<. It should be noted that the ring Ar b< in the above formula has two nitrogen atoms and one boron atom. Therefore, the expression "aromatic ring system having 5 to 60 aromatic ring atoms" clarifies that essential parts of the ring Ar b< do not have to have any heteroatoms, or the components not explicitly mentioned may represent an aromatic ring system having 5 to 60 aromatic ring atoms.Accordingly, it can be provided that the ring Ar b< comprises a group Ar b< , as well as two nitrogen atoms and one boron atom. The group Ar b< stands on each occurrence, identically or differently, for an aromatic or heteroaromatic ring system having 5 to 50 aromatic ring atoms, which may be substituted by one or more radicals Ar or R b<, where the group Ar b< can form a ring system with a group R, Ar or Z c< or the rings Ar a< and the group Ar b< together can form a ring system. Preferably, the ring Ar b< is formed by a group Ar b< and the two nitrogen atoms and the boron atom, where this ring formed by the group Ar b<, the group Ar b<, the two nitrogen atoms and the boron atom preferably comprises five to eight, particularly preferably five or six ring atoms.The Ar b< group bonds to the other atoms of the ring formed by the Ar b< group, the two nitrogen atoms, and the boron atom, preferably via two adjacent C atoms that are part of an aromatic or heteroaromatic group. If the ring formed by the Ar b< group, the two nitrogen atoms, and the boron atom comprises more than 5 ring atoms, the other residues can be considered part of the Ar b< group, which does not necessarily contain only aryl or heteroaryl groups.

[0019] An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 2 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.

[0020] An electron-poor heteroaryl group within the meaning of the present invention is a heteroaryl group that has at least one heteroaromatic six-membered ring containing at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to this six-membered ring. Examples of electron-poor heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, or quinoxaline.

[0021] An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be linked by a non-aromatic unit, such as a C, N, or O atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.are understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a short alkyl group. The aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine, or groups in which two or more aryl and / or heteroaryl groups are linked by single bonds.

[0022] In the context of the present invention, an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 20 C atoms and in which individual H atoms or CH 2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl or octynyl.Unter einer Alkoxygruppe mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe mit 1 bis 40 C-Atomen werden insbesondere Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n-Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluormethylthio, Pentafluorethylthio, 2,2,2-Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio verstanden.In general, alkyl, alkoxy, or thioalkyl groups according to the present invention may be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH 2 groups may be replaced by the above-mentioned groups; furthermore, one or more H atoms may also be replaced by D, F, Cl, Br, I, CN, or NO 2 , preferably F, Cl, or CN, more preferably F or CN, particularly preferably CN.

[0023] An aromatic or heteroaromatic ring system with 5 - 60 or 5 to 40 aromatic ring atoms, which may each be substituted by the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring via any position, is understood to mean in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, Thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Gruppen,which are derived from combinations of these systems.,

[0024] For the purposes of this description, the phrase "two or more residues can form a ring" is understood to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0025] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:

[0026] In a preferred embodiment, the compounds according to the invention can comprise a structure of the formulas (II-1) to (II-18), particularly preferably the compounds according to the invention can be selected from the compounds of the formulas (II-1) to (II-18), where the symbols R, Ar, Ar a< and Ar b< have the meanings given above, in particular for formula (I), and X, identically or differently on each occurrence, represents N or CR, preferably CR. In formulas (II-17) and (II-18), the ring Ar b< is preferably formed by a group Ar b<, the nitrogen atom, the boron atom, and the carbon atom, the further preferences of this ring corresponding to those set out above.

[0027] Structures / compounds of the formulas (II-5) to (II-16) are preferred, structures / compounds of the formulas (II-9) to (II-16) are particularly preferred, structures / compounds of the formulas (II-13) to (II-16) are especially preferred, and structures / compounds of the formulas (II-13) and (II-14) are very particularly preferred.

[0028] Furthermore, structures / compounds of the formulas (II-1), (II-3), (II-5), (II-7), (II-9), (II-11), (II-13) and (II-15) are preferred over comparable structures / compounds of the formulas (II-2), (II-4), (II-6), (II-8), (II-10), (II-12), (II-14) and (II-16). Structures or compounds are comparable in particular if they have essentially the same substituents and / or substitution patterns, where essentially the same means that the position of the carbonyl group relative to the boron atom is disregarded. This preference also applies to the structures and / or compounds presented below; unless otherwise stated.

[0029] If a compound contains two or more nitrogen atoms, these nitrogen atoms are preferably not adjacent, so that no N—N bonds are present, apart from the N—N bond in formula (I) or the preferred embodiments of this structure / compound presented above and below.

[0030] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise a structure of the formulas (III-1) to (III-48), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (III-1) to (III-48), where the symbols Ar and R have the meanings set out above, in particular for formula (I), and the following applies to the other symbols: X, identical or different on each occurrence, is N or CR, preferably CR, with the proviso that no more than two of the groups X in a cycle are N, where R has the meaning set out above, in particular for formula (I); X a<, identical or different on each occurrence, is N or CR a<, preferably CR a<, with the proviso that no more than two of the groups X a< in a cycle are N, where R a< has the meaning set out above, in particular for formula (I);X b< is, identical or different on each occurrence, N or CR b< , preferably CR b< , with the proviso that no more than two of the groups X b< in a cycle are N, where R b< has the meaning set out above, in particular for formula (I), Y 1< is, identical or different on each occurrence, a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably a bond, N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), B(Ar), B(R), C(R) 2 , C=O, O or S, where R has the meaning set out above, in particular for formula (I);Y 2< is on each occurrence, identically or differently, a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably a bond, N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , especially preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);Y 3< is the same or different in every occurrence C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I); Y 4< is on each occurrence, identically or differently, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, C(R) 2 , Si(R) 2 , O or S, preferably N(Ar), N(R) or O, S, particularly preferably N(Ar) or O, where R has the meaning set out above, in particular for formula (I);Y 5 < is the same or different in every occurrence C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);Y 6< is the same or different in every occurrence C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);

[0031] Structures / compounds of the formulas (III-3) to (III-14), (III-17) to (III-26), (III-47) and (III-48) are preferred and structures of the formulas (III-3), (III-5), (III-7), (III-9), (III-11), (III-13), (III-17), (III-19), (III-21), (III-23), (III-25) and (III-47) are particularly preferred.

[0032] Preferably, in particular in formulas (III-1) to (III-48), it can be provided that not more than four, preferably not more than two groups X, X a< and X b< stand for N, particularly preferably all groups X, X a< and X b< stand for CR, CR a< or CR b<.

[0033] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise a structure of the formulas (IV-1) to (IV-48), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IV-1) to (IV-48), where the symbols R, R a< and R b< have the meanings given above, in particular for formula (I), the symbols Y 1< , Y 2< , Y 3< , Y 4< , Y 5< and Y 6< have the meanings given above, in particular for formulas (III-1) to (III-48) and the following applies to the other symbols: l is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1, k is 0 or 1.

[0034] Structures / compounds of the formulas (IV-3) to (IV-14), (IV-17) to (IV-26), (IV-47) and (IV-48) are preferred and structures of the formulas (IV-3), (IV-5), (IV-7), (IV-9), (IV-11), (IV-13), (IV-17), (IV-19), (IV-21), (IV-23), (IV-25) and (IV-47) are particularly preferred.

[0035] The sum of the indices k, j, m, n and l is at most, in particular in structures / compounds of the formulas (IV-1) to (IV-48), preferably at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.

[0036] Furthermore, in formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48) and / or the preferred embodiments of these formulas set out below, it can be provided that at least one radical R, R a< , R b< represents a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group can each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups are substituted by R 1< C=CR 1<, C≡C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , -C(=O)O-, -C(=O)NR 1< -, NR 1< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms,which may be substituted by one or more radicals R 1<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; or a heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<.

[0037] Preferably, inter alia, in formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48) and / or the preferred embodiments of these formulas set out below, it can be provided that at least one radical R, R a< , R b< represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<, or represents an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<;or represents a heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or represents a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or represents an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<, particularly preferably represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<.;

[0038] Furthermore, it can preferably be provided that the structures / compounds of formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48) and / or the preferred embodiments of these formulas set out below have at most one, preferably no, free olefin-like double bond, with aromatic 6-membered rings preferably being fused to aromatic 5-membered rings. Free olefin-like double bonds are, first of all, -C=C- groups that are not part of an aromatic or heteroaromatic system and preferably contain hydrogen atoms. In addition, free olefin-like double bonds are -C=C- groups that are part of a heteroaromatic 5-membered ring, as realized, for example, in furan or imidazole residues, whereby these groups must be free. This is particularly the case if the carbon atoms of the CC double bond are bonded to a hydrogen atom.In the case of condensation of another aromatic or heteroaromatic ring, as occurs, for example, with dibenzofuran or benzimidazole residues, no olefin-like double bonds are present, since the -C=C- groups are not present freely. Furthermore, no olefin-like double bonds are present if the two carbon atoms of the CC double bond are connected by a ring, which is preferably formed by the groups of formulas (RA-1) to (RA-12), formulas (RA-1a) to (RA-4f), and / or formula (RB) described below.

[0039] Furthermore, it can preferably be provided that the structures / compounds of the formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48) and / or the preferred embodiments of these formulas set out below do not have structures with 7-ring atoms, with the exception of bridged structures, in particular bicycles and tricycles.

[0040] In a preferred development of the present invention, it can be provided that at least two radicals R, R a< , R b< form a condensed ring with the further groups to which the two radicals R, R a< , R b< are bonded, wherein the two radicals R, R a< , R b< form at least one structure of the formulas (RA-1) to (RA-12) where R 1< has the meaning set out above, the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< bind to the other groups, and the other symbols have the following meaning: Y 7< is, identically or differently at each occurrence, C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), NR 1< , NAr', O or S, preferably C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), O or S;R c< is, identically or differently at each occurrence, F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may each be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups are substituted by R 2< C=CR 2< , C=C, Si(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , -C(=O)O-, -C(=O)NR 2< -, NR 2< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2<;two radicals R c< can also form a ring system with one another or one radical R c< can form a ring system with one radical R 1< or with another group; s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2.

[0041] In a preferred embodiment of the invention, the at least two radicals R, R a< , R b< form a condensed ring with the further groups to which the two radicals R, R a< , R b< are bonded, wherein the two radicals R, R a< , R b< preferably form at least one of the structures of the formulas (RA-1a) to (RA-4f) where the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< bind to the further groups, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the symbols R 1< , R 2< , R c< and the indices s and t have the meaning set out above, in particular for formula (I) and / or formulas (RA-1) to (RA-12).

[0042] Furthermore, it can be provided that the at least two radicals R, R a< , R b< , which form structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and form a condensed ring, represent radicals R, R a< , R b< from adjacent groups X, X a< , X b< or represent radicals R, R a< , R b< which each bind to adjacent C atoms, wherein these C atoms are preferably connected via a bond.

[0043] In a further preferred embodiment, at least two radicals R, R a< , R b< form a condensed ring with the further groups to which the two radicals R, R a< , R b< are bonded, wherein the two radicals R, R a< , R b< form structures of the formula (RB), where R 1< has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< bind to the further groups, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 8< is C(R 1< ) 2 , NR 1< , NAr', BR 1< , BAr', O or S, preferably C(R 1< ) 2 , NAr' or O.

[0044] It can be provided that the at least two radicals R, R a< , R b< , which form structures of the formula (RB) and form a condensed ring, represent radicals R, R a< , R b< from adjacent groups X, X a< , X b< , or represent radicals R, R a< , R b< which each bind to adjacent C atoms, wherein these C atoms are preferably connected to one another via a bond.

[0045] Particularly preferably, the compounds comprise at least one structure of the formulas (V-1) to (V-12), particularly preferably the compounds are selected from compounds of the formulas (V-1) to (V-12), wherein the compounds have at least one condensed ring, where the symbols R a< , R b< , Y 2< and Y 5< have the meanings given above, in particular for formula (I) and / or formulas (III-1) to (III-48), the symbol o stands for the attachment points and the other symbols have the following meaning: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1.

[0046] The compounds particularly preferably comprise at least one structure of the formulas (VI-1) to (VI-12), particularly preferably the compounds are selected from compounds of the formulas (VI-1) to (VI-12), wherein the compounds have at least one condensed ring where the symbols R, R a< , R b< , Y 2< and Y 5< have the meanings given above, in particular for formula (I) and / or formulas (III-1) to (III-48), the symbol o stands for the attachment points of the condensed ring and the other symbols have the following meaning: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1.

[0047] Preferably, the condensed ring, in particular in formulas (V-1) to (V-12) and / or (VI-1) to (VI-12), is formed by at least two radicals R, R a< , R b< and the further groups to which the two radicals R, R a< , R b< are bonded, wherein the at least two radicals R, R a< , R b< form structures of the formulas (RA-1) to (RA-12) and / or of the formula (RB), preferably structures of the formulas (RA-1) to (RA-12).

[0048] Preferably, the compounds may have at least two condensed rings, wherein at least one condensed ring is formed by structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and a further ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB).

[0049] Particularly preferably, the compounds comprise at least one structure of the formulas (VII-1) to (VII-12), particularly preferably the compounds are selected from compounds of the formulas (VII-1) to (VII-12), wherein the compounds have at least two condensed rings, where the symbols R a< , R b< , Y 2< and Y 5< have the meanings given above, in particular for formula (I) and / or formulas (III-1) to (III-48), the symbol o stands for the attachment points and the other symbols have the following meaning: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1.

[0050] Preferably, at least one of the condensed rings, particularly preferably both of the condensed rings, in particular in formulas (VII-1) to (VII-12), are formed by at least two radicals R, R a< , R b< and the further groups to which the two radicals R, R a< , R b< are bonded, wherein the at least two radicals R, R a< , R b< form structures of the formulas (RA-1) to (RA-12) and / or of the formula (RB), preferably structures of the formulas (RA-1) to (RA-12).

[0051] In particular in the formulas (V-1) to (V-12), (VI-1) to (VI-12) and / or (VII-1) to (VII-12), it can be provided that the sum of the indices j, n and m is preferably 0, 1, 2 or 3, particularly preferably 1 or 2.

[0052] Furthermore, it can be provided that the substituents R, R a< , R b< , R c< , R 1< and R 2< according to the above formulas do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system to which the substituents R, R a< , R b< , R c< , R 1< and R 2< are bonded. This includes the formation of a condensed aromatic or heteroaromatic ring system with possible substituents R 1< and R 2<, which can be bonded to the radicals R, R a< , R b< , R c< and R 1<.

[0053] If two radicals, which can in particular be selected from R, Ra< , Rb< , Rc< , R1< and / or R2< , form a ring system with one another, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic. The radicals which form a ring system with one another can be adjacent, i.e. these radicals are bonded to the same carbon atom or to carbon atoms which are directly bonded to one another, or they can be further apart from one another. Furthermore, the ring systems provided with the substituents R, Ra< , Rb< , Rc< , R1< and / or R2< can also be linked to one another via a bond, so that a ring closure can be brought about. In this case, each of the corresponding bonding sites is preferably provided with a substituent R, Ra< , Rb< , Rc< , R1< and / or R2<.

[0054] According to a preferred embodiment, a compound according to the invention can be represented by at least one of the structures according to formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48), (V-1) to (V-12), (VI-1) to (VI-12) and / or (VII-1) to (VII-12). Preferably, compounds according to the invention, preferably comprising structures according to formulas (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48), (V-1) to (V-12), (VI-1) to (VI-12) and / or (VII-1) to (VII-12) have a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and very particularly preferably less than or equal to 1200 g / mol.

[0055] Furthermore, preferred compounds according to the invention are characterized by their sublimability. These compounds generally have a molecular weight of less than approximately 1200 g / mol.

[0056] Preferably, it can be provided that Ar a< is selected, identically or differently on each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which may each be substituted by one or more radicals Ar or R a<.

[0057] A structure according to formula (I) can comprise a ring Ar b< which, on each occurrence, is the same or different, and represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals Ar or R b<, where the ring Ar b< can form a ring system with a group R, Ar or Z c<, or the rings Ar a< and Ar b< together can form a ring system. Accordingly, the ring Ar b< can comprise a group Ar b< which, on each occurrence, is the same or different, and represents an aromatic or heteroaromatic ring system having 5 to 50 aromatic ring atoms which may be substituted by one or more radicals Ar or R b<. This group Ar b< forms a ring with the two nitrogen atoms and the boron atom, preferably with five to eight, particularly preferably five or six, ring atoms.Furthermore, it can preferably be provided that the group Ar b< is selected, identically or differently on each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which may each be substituted by one or more radicals Ar or R b<.

[0058] Preferred aromatic or heteroaromatic ring systems R, R a< , R b< , R c< , Ar' and / or Ar are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3-, 4- or 9-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, Dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene,which may each be substituted by one or more radicals R 1< or R.,

[0059] Preferably, it can be provided that at least one substituent R, R a< , R b< is selected, identically or differently on each occurrence, from the group consisting of H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-78, preferably the substituents R, R a< , R b< either form a condensed ring, preferably according to the structures of the formulas (RA-1) to (RA-12) or (RB) or the substituent R, R a< , R b< is selected, identically or differently on each occurrence, from the group consisting of H, D or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-78, and / or the group Ar' is selected, identically or differently on each occurrence, from the groups of the following formulas Ar-1 to Ar-78, where R 1< has the meanings given above, the dashed bond represents the attachment point and furthermore: Ar 1< is, on each occurrence, the same or different, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<; A is, on each occurrence, the same or different, C(R 1<) 2 , NR 1< , O or S; p is 0 or 1, where p = 0 means that the group Ar 1< is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding radical, q is 0 or 1, where q = 0 means that no group A is bonded to this position and radicals R 1< are bonded to the corresponding carbon atoms instead.

[0060] Structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) are preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.

[0061] If the above-mentioned groups for structures of formulas (Ar-1) to (Ar-78) have multiple A groups, all combinations from the definition of A are possible. Preferred embodiments are then those in which one A group represents NR 1< and the other A group represents C(R 1< ) 2 or in which both A groups represent NR 1< or in which both A groups represent O.

[0062] When A stands for NR 1<, the substituent R 1< which is bonded to the nitrogen atom preferably stands for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2<. In a particularly preferred embodiment, this substituent R 1<, identical or different on each occurrence, stands for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms, which does not have any fused aryl groups and which does not have any fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-membered ring groups are directly fused to one another, and which may in each case also be substituted by one or more radicals R 2<.Phenyl, biphenyl, terphenyl, and quaterphenyl with linkage patterns as listed above for Ar-1 to Ar-11 are preferred, where these structures may be substituted by one or more R 2< radicals instead of R 1<, but are preferably unsubstituted. Also preferred are triazine, pyrimidine, and quinazoline, as listed above for Ar-47 to Ar-50, Ar-57, and Ar-58, where these structures may be substituted by one or more R 2< radicals instead of R 1<.

[0063] Preferred substituents R, R a< , R b< and R c< are described below.

[0064] In a preferred embodiment of the invention, R, R a< , R b< are the same or different on each occurrence and are selected from the group consisting of H, D, F, CN, NO 2 , Si(R 1< ) 3 , B(OR 1< ) 2 , a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<.

[0065] In a further preferred embodiment of the invention, substituent R, R a< , R b< is the same or different on each occurrence and is selected from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<.

[0066] Furthermore, it can be provided that at least one substituent R, R a< , R b< is selected, identically or differently on each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a group N(Ar') 2 . In a further preferred embodiment of the invention, the substituents R, R a< , R b< either form a ring according to the structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB) or the substituent R, R a< , R b< is selected, identically or differently on each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a group N(Ar') 2 .Particularly preferably, substituent R, R a< , R b< is the same or different on each occurrence and is selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, which may each be substituted by one or more radicals R 1<.

[0067] Preferably, it can be provided that at least one substituent R, R a< , R b< is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which may each be substituted by one or more radicals R 1<. Here, the term substituent means in particular that R, R a< , R b< are not equal to H. Furthermore, the substituents R, R a< , R b< can be the same or different if two or more substituents are present which are selected from the aforementioned aromatic or heteroaromatic group.

[0068] In a further embodiment, it can be provided that at least one substituent R, R a< , R b< is selected from o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenylpyrimidin-2-yl, 4,6-diphenyltrianin-2-yl, naphthalene, phenanthrene, chrysene, spirobifluorene, triphenylene, anthracene, benzanthracene, fluorene and / or pyrene, which may each be substituted by one or more radicals R 1<. Preferred radicals here are spirobifluorene, o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenylpyrimidin-2-yl and 4,6-diphenyltrianin-2yl. The substituents R, R a< , R b< may be the same or different if two or more substituents are present which are selected from the aromatic group mentioned.

[0069] Structures / compounds with a group selected from o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenyl-pyrimidin-2-yl, 4,6-diphenyl-trianin-2-yl, naphthalene, phenanthrene, chrysene, spiro-bifluorene, triphenylene, anthracene, benzanthracene, fluorene and / or pyrene are particularly suitable for use as electron transport material and / or as matrix material.

[0070] In a preferred embodiment of the invention, R c< is the same or different on each occurrence and is selected from the group consisting of a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.

[0071] In a further preferred embodiment of the invention, R c< is the same or different on each occurrence and is selected from the group consisting of a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may be substituted in each case by one or more radicals R 2<, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 2<.Particularly preferably, R c< is selected, identically or differently on each occurrence, from the group consisting of a straight-chain alkyl group having 1 to 5 C atoms or a branched or cyclic alkyl group having 3 to 5 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2< or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.

[0072] In a preferred embodiment of the invention, R c< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1 to 6 C atoms or a cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<; two radicals R c< may also form a ring system with one another.Particularly preferably, R c< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, in particular having 6 aromatic ring atoms, which may in each case be substituted by one or more, preferably non-aromatic radicals R 2<, but is preferably unsubstituted; two radicals R c< can form a ring system with one another. Very particularly preferably, R c< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms, or a branched alkyl group having 3 to 6 C atoms.Most preferably, R c< represents a methyl group or a phenyl group, where two phenyl groups together can form a ring system, with a methyl group being preferred over a phenyl group.

[0073] Preferred aromatic or heteroaromatic ring systems for which substituents R, R a< , R b< , R c< or Ar or Ar' stand are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, Dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline,Phenanthrene or triphenylene, which may each be substituted by one or more radicals R, R 1< or R 2<. The structures Ar-1 to Ar-78 listed above are particularly preferred, with structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) being preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) being particularly preferred. With regard to the structures Ar-1 to Ar-78, it should be noted that these are represented with a substituent R 1<. In the case of the ring systems Ar, these substituents R 1< are to be replaced by R and in the case of R c< these substituents R 1< are to be replaced by R 2<.

[0074] Further suitable groups R, R a< , R b< are groups of the formula -Ar 4< -N(Ar 2< )(Ar 3< ), where Ar 2< , Ar 3< and Ar 4<, identical or different on each occurrence, represent an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<. The total number of aromatic ring atoms of Ar 2< , Ar 3< and Ar 4< is a maximum of 60 and preferably a maximum of 40.

[0075] Ar 4< and Ar 2< can be linked to one another and / or Ar 2< and Ar 3< can also be linked to one another by a group selected from C(R 1< ) 2 , NR 1< , O, or S. Preferably, Ar 4< and Ar 2< are linked to one another, or Ar 2< and Ar 3< are linked to one another, in each case ortho to the position of the linkage to the nitrogen atom. In a further embodiment of the invention, none of the groups Ar 2< , Ar 3<, or Ar 4< are linked to one another.

[0076] Preferably, Ar 4< is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, each of which may be substituted by one or more R 1< radicals. Ar 4< is particularly preferably selected from the group consisting of ortho-, meta-, or para-phenylene or ortho-, meta-, or para-biphenyl, each of which may be substituted by one or more R 1< radicals, but is preferably unsubstituted. Most preferably, Ar 4< is an unsubstituted phenylene group.

[0077] Preferably, Ar 2< and Ar 3<, identical or different on each occurrence, are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may each be substituted by one or more radicals R 1<. Particularly preferred groups Ar 2< and Ar 3< are, identically or differently at each occurrence, selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-, 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-dibenzothiophene, indenocarbazole, indolocarbazole, 2-, 3- or 4-pyridine, 2-, 4- or 5-pyrimidine, Pyrazine, pyridazine, triazine, phenanthrene or triphenylene, each of which may be substituted by one or more radicals R 1<.Very particularly preferably, Ar 2< and Ar 3< are selected, identically or differently on each occurrence, from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, in particular 1-, 2-, 3- or 4-fluorene, or spiro-bifluorene, in particular 1-, 2-, 3- or 4-spirobifluorene.

[0078] In a further preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.In a particularly preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, from the group consisting of H, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may be substituted by one or more radicals R 5<, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more radicals R 5<, but is preferably unsubstituted.

[0079] In a further preferred embodiment of the invention, R 2< is identical or different on each occurrence and is H, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted.

[0080] In compounds according to the invention that are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds that are processed from solution, compounds substituted by alkyl groups, especially branched alkyl groups, with up to 10 carbon atoms, or substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups, are also suitable.

[0081] Furthermore, it can be provided that the compound comprises exactly two or exactly three structures according to formula (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48), (V-1) to (V-12), (VI-1) to (VI-12) and / or (VII-1) to (VII-12).

[0082] In a preferred embodiment, the compounds are selected from compounds of the formulas (D-1) to (D-17), where the group L' represents a linking group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, and the further symbols used have the meanings given above, in particular for formula (I) and / or formulae (II-1) to (II-18).

[0083] In a further preferred embodiment of the invention, L 1< represents a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning given above, in particular for formula (I). More preferably, L' represents an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, where R 2< may have the meaning given above, in particular for formula (I).

[0084] Furthermore, the symbol L' shown inter alia in formula (D17) is preferably identical or different on each occurrence and represents a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0085] Furthermore, it can be provided that the group L 1< shown in formula (D17) comprises an aromatic ring system with at most four, preferably at most three, particularly preferably at most two, fused aromatic and / or heteroaromatic 6-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures.

[0086] Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0087] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, which may each be substituted by one or more radicals R 1<, but are preferably unsubstituted.

[0088] The above-mentioned preferred embodiments can be combined with each other as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0089] Examples of preferred compounds according to the embodiments listed above are the compounds listed in the following table: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87

[0090] Preferred embodiments of compounds according to the invention are explained in more detail in the examples, whereby these compounds can be used alone or in combination with others for all purposes according to the invention.

[0091] Provided that the conditions stated in claim 1 are met, the above-mentioned preferred embodiments can be combined with one another in any way. In a particularly preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

[0092] The compounds of the invention can, in principle, be prepared by various methods. However, the methods described below have proven particularly suitable.

[0093] Therefore, a further subject of the present invention is a process for preparing the compounds according to the invention, in which a basic skeleton with at least one of the groups W a< or a precursor of one of the groups W a< is synthesized and an aromatic or heteroaromatic radical is introduced by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0094] Suitable compounds comprising a basic skeleton with a group W a< can often be obtained commercially, the starting compounds presented in the examples being obtainable by known processes, so that reference is made thereto.

[0095] These compounds can be reacted with other compounds by known coupling reactions, the necessary conditions for this being known to the person skilled in the art and detailed information in the examples assisting the person skilled in the art in carrying out these reactions.

[0096] Particularly suitable and preferred coupling reactions, all of which lead to CC and / or CN bond formations, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, and HIYAMA. These reactions are widely known, and the examples provide further guidance to the skilled person.

[0097] The compounds of the invention can be prepared, inter alia, according to Scheme 1 and Scheme 2. Scheme 1 specifically illustrates the preparation of compounds of the invention starting from hydrazine derivatives, demonstrating a possible formation of a ring Ar b<, as present in preferred compounds. Scheme 2 describes a synthesis via a carboxylic acid derivative that does not contain a hydrazine group. Rather, this group is formed by reacting a nitro group with an amino group.

[0098] The meaning of the symbols used in Schemes 1 and 2 essentially corresponds to that defined for formula (I) or preferred embodiments of these structures, although numbering and a complete representation of all symbols have been omitted for reasons of clarity. Furthermore, for reasons of clarity, the use of symbols to represent possible nitrogen atoms in the heteroaromatic rings has often been omitted, as they are represented in particular in formulas (I), (II-1) to (II-18) and / or (III-1) to (III-48) by the symbols X, X a< and X b<. These details are therefore to be understood as examples, and the person skilled in the art is able to transfer the syntheses presented above and below, in particular in the examples, to compounds in which one or more of the symbols X, X a< and X b< stand for nitrogen.

[0099] The principles of the preparation processes described above are, in principle, known from the literature for similar compounds and can be easily adapted by those skilled in the art to prepare the compounds of the invention. Further information can be found in the examples.

[0100] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1< H-NMR and / or HPLC).

[0101] The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid, or boronic acid esters, or by reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality, or via the polymerizable group, respectively. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as crosslinked or uncrosslinked layers.

[0102] The invention therefore further provides oligomers, polymers or dendrimers comprising one or more of the above-listed structures of the formula (I) and preferred embodiments of this formula or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of the formula (I) and preferred embodiments of this formula to the polymer, oligomer or dendrimer are present. Depending on the linkage of the structures of the formula (I) and preferred embodiments of this formula or of the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated. The oligomers or polymers can be linear, branched or dendritic.The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.

[0103] To prepare the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other monomers. Copolymers are preferred, wherein the units according to formula (I) or the preferred embodiments described above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%. Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (e.g. according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g. according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g. according to WO 92 / 18552), carbazoles (e.g. according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g. according to WO 2004 / 041901 or WO 2004 / 113412), ketones (e.g. according to WO 2005 / 040302), phenanthrenes (e.g.according to WO 2005 / 104264 or WO 2007 / 017066) or several of these units. The polymers, oligomers, and dendrimers may contain further units, for example hole-transport units, in particular those based on triarylamines, and / or electron-transport units.

[0104] Of particular interest are also compounds according to the invention that are characterized by a high glass transition temperature. In this context, particular preference is given to compounds according to the invention comprising structures according to formula (I) or the preferred embodiments described above and below, which have a glass transition temperature of at least 70°C, more preferably of at least 110°C, most preferably of at least 125°C, and especially preferably of at least 150°C, determined according to DIN 51005 (version 2005-08).

[0105] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, Decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetol,1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0106] The present invention therefore further provides a formulation or a composition comprising at least one compound according to the invention and at least one further compound. The further compound can, for example, be a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation. However, the further compound can also be at least one further organic or inorganic compound which is likewise used in the electronic device, for example an emitter and / or a matrix material, wherein these compounds differ from the compounds according to the invention. Suitable emitters and matrix materials are listed below in connection with the organic electroluminescent device. The further compound can also be polymeric.

[0107] The present invention therefore further provides a composition comprising a compound according to the invention and at least one further organic functional material. Functional materials are generally the organic or inorganic materials that are introduced between the anode and cathode. The organic functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF (thermally activated delayed fluorescence), host materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials, hole-blocking materials, wide-band-gap materials, and n-dopants.

[0108] The present invention further provides for the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device, preferably as an emitter, particularly preferably as a green, red, or blue emitter. Compounds according to the invention preferably exhibit fluorescent properties and thus preferably provide fluorescent emitters.

[0109] Preferably, it can be provided that structures / compounds according to formulas (II-2) to (II-8), (II-17) to (II-23), (III-2) to (III-8), (III-17) to (III-23), (IV-2) to (IV-8), (IV-17) to (IV-23), (V-1), (V-2), (V-5) and / or (V-6) are used as emitters.

[0110] Furthermore, compounds according to formula (I) or an oligomer, polymer, or dendrimer comprising structures according to formula (I) can be used as host materials and / or electron transport materials. Preferably, it can be provided that structures / compounds with an anthracene group (Ar-76) to (Ar-78), preferably (Ar-78), and / or compounds according to formulas (II-9), (II-10), (II-24), (II-25), (III-9), (III-10), (III-24), (III-25), (IV-9), (IV-10), (IV-24) and / or (IV-25) are used as electron transport material and / or matrix material.

[0111] The present invention further relates to an electronic device comprising at least one compound according to the invention. An electronic device within the meaning of the present invention is a device that contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0112] The electronic device is preferably selected from the group consisting of Particularly preferred electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), "organic plasmon emitting devices" (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), in particular phosphorescent OLEDs.

[0113] The organic electroluminescent device contains a cathode, an anode, and at least one emitting layer. In addition to these layers, it may contain further layers, for example, one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers, and / or charge-generation layers. Interlayers, which, for example, have an exciton-blocking function, may also be inserted between two emitting layers. It should be noted, however, that not all of these layers are necessarily present. The organic electroluminescent device may contain one emitting layer or it may contain multiple emitting layers.If multiple emission layers are present, they preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, particularly for white-emitting OLEDs.

[0114] The compound according to the invention can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device comprising a structure / compound according to formula (I) or the preferred embodiments outlined above in an emitting layer as an emitter, preferably a red, green, or blue emitter. Very preferred is an organic electroluminescent device comprising a structure / compound according to formula (I) or the preferred embodiments outlined above in an emitting layer as a fluorescent blue emitter. In this case, compounds structures / compounds according to formulas (II-9) to (II-16), (III-3) to (III-14), (III-17) to (III-26), (III-47) and (III-48) are particularly preferred and structures / compounds of the formulas (III-3), (III-5), (III-7), (III-9), (III-11), (III-13), (III-17), (III-19), (III-21), (III-23), (III-25) and (III-47) are particularly preferred.

[0115] When the compound according to the invention is used as an emitter in an emitting layer, a suitable matrix material (also called host material) is preferably used, which is known as such.

[0116] A preferred mixture of the compound according to the invention and a matrix material contains between 99 and 1 vol.%, preferably between 98 and 10 vol.%, particularly preferably between 97 and 60 vol.%, in particular between 95 and 80 vol.% of matrix material, based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 vol.%, preferably between 2 and 90 vol.%, particularly preferably between 3 and 40 vol.%, in particular between 5 and 20 vol.% of the emitter, based on the total mixture of emitter and matrix material.

[0117] Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-bis-carbazolylbiphenyl) or those in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. B. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. B. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. B. according to WO 2007 / 137725, silanes, e.g. B. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. B. according to WO 2006 / 117052, triazine derivatives, e.g.according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. B. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. B. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. B. according to JP 3139321 B2.

[0118] Furthermore, a compound that does not participate, or does not participate to a significant extent, in charge transport can be used as a co-host, as described, for example, in WO 2010 / 108579. Particularly suitable co-matrix materials in combination with the compound according to the invention are compounds that have a large band gap and do not participate, or at least do not participate to a significant extent, in the charge transport of the emitting layer. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or WO 2010 / 006680.

[0119] In a preferred embodiment, a compound containing a structure / compound according to formula (I) or the preferred embodiments described above, which is used as an emitter, is preferably used in combination with one or more phosphorescent materials (triplet emitters) and / or a compound that represents a TADF (thermally activated delayed fluorescence) host material. This preferably forms a hyperfluorescence system as described in WO 2012 / 133188 and / or a hyperphosphorescence system as described in US 2017271611. This combination represents a preferred composition according to the present invention.

[0120] WO 2015 / 091716 A1 and WO 2016 / 193243 A1 disclose OLEDs containing both a phosphorescent compound and a fluorescent emitter in the emission layer, with the energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound therefore behaves like a host material. As those skilled in the art know, host materials have higher singlet and triplet energies than the emitters, so that the energy of the host material is transferred to the emitter as optimally as possible. The systems disclosed in the prior art exhibit precisely such an energy relationship.

[0121] For the purposes of this invention, phosphorescence refers to luminescence from an excited state with higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state. For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are considered phosphorescent compounds.

[0122] Particularly suitable phosphorescent compounds (= triplet emitters) are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferably used as phosphorescent emitters, in particular compounds containing iridium or platinum.

[0123] Examples of the emitters described above can be found in the applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 001990, WO 2018 / 019687, WO 2018 / 019688, WO 2018 / 041769, WO 2018 / 054798, WO 2018 / 069196, WO 2018 / 069197, WO 2018 / 069273, WO 2018 / 178001, WO 2018 / 177981, WO 2019 / 020538, WO 2019 / 115423, WO 2019 / 158453 and WO 2019 / 179909.In general, all phosphorescent complexes as used according to the prior art for phosphorescent electroluminescent devices and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.

[0124] A compound according to the invention can preferably be used in combination with a TADF host material and / or a TADF emitter, as previously explained.

[0125] The process known as thermally activated delayed fluorescence (TADF) is described, for example, by BH Uoyama et al., Nature 2012, Vol. 492, 234. To enable this process, a comparatively small singlet-triplet separation ΔE(S 1 - T 1 ) of, for example, less than about 2000 cm -1 is required in the emitter. To open the inherently spin-forbidden transition T 1 → S 1 , another compound can be provided in the matrix next to the emitter. This compound exhibits strong spin-orbit coupling, enabling inter-system crossing through the spatial proximity and the resulting interaction between the molecules. Alternatively, the spin-orbit coupling can be generated via a metal atom contained in the emitter.

[0126] Further valuable information on hyperfluorescence systems is provided in WO2012 / 133188 (Idemitsu), WO2015 / 022974 (Kyushu Univ.), WO2015 / 098975 (Idemitsu), WO2020 / 053150 (Merck) and DE202019005189 (Merck), among others.

[0127] Further valuable information on hyperphosphorescence systems is provided, among others, in WO2015 / 091716 A1, WO2016 / 193243 A1 (BASF), WO01 / 08230 A1 (Princeton Univ. (Mark Thompson)), US2005 / 0214575A1 (Fuji), WO2012 / 079673 (Merck), WO2020 / 053314 (Merck) and WO2020 / 053315 (Merck).

[0128] In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole-injection layer and / or hole-transport layer and / or hole-blocking layer and / or electron-transport layer, i.e., the emitting layer directly adjoins the hole-injection layer or the anode, and / or the emitting layer directly adjoins the electron-transport layer or the electron-injection layer or the cathode, as described, for example, in WO 2005 / 053051. Furthermore, it is possible to use a metal complex that is the same as or similar to the metal complex in the emitting layer as a hole-transport or hole-injection material directly adjacent to the emitting layer, as described, for example, in WO 2009 / 030981.

[0129] Furthermore, an organic electroluminescent device is preferred, comprising a structure / compound according to formula (I) or the preferred embodiments described above in an electron-conducting layer as the electron-transport material. Compounds containing an anthracene group, preferably a group according to formulas (Ar-76) to (Ar-78), are particularly preferred.

[0130] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be used. Therefore, the skilled person can, without inventive step, use all materials known for organic electroluminescent devices in combination with the structure / compound according to formula (I) or the preferred embodiments described above.

[0131] Also preferred is an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, it is also possible for the initial pressure to be even lower, for example, less than 10 -7 mbar.

[0132] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus patterned.

[0133] Also preferred is an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0134] Formulations for applying a compound according to formula (I) or the preferred embodiments thereof set out above are novel. A further subject of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof set out above.

[0135] Furthermore, hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.

[0136] These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices containing the compounds according to the invention.

[0137] The compounds of the invention and the organic electroluminescent devices of the invention are distinguished from the prior art, in particular by an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good. In a further variant, the compounds of the invention and the organic electroluminescent devices of the invention are distinguished from the prior art, in particular by improved efficiency and / or operating voltage and a longer lifetime.

[0138] The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices comprising structures / compounds according to formula (I) or the preferred embodiments set out above and below as emitters, have very narrow emission bands with low FWHM (Full Width Half Maximum) values ​​and lead to particularly color-pure emission, as can be recognized by the small CIE y values. What is particularly surprising here is that both blue emitters with low FWHM values ​​and emitters with low FWHM values ​​are provided which emit in the green, yellow or red region of the color spectrum. 2. The structures / compounds according to formula (I) according to the invention or the preferred embodiments set out above and below display very high stability and lifetime. 3. With structures / compounds according to formula (I) orThe preferred embodiments described above and below prevent the formation of optical loss channels in electronic devices, particularly organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. Exciton energy is typically transferred from a matrix or host in the emission layer to the emitter either via so-called Dexter or Förster transfer. Förster energy transfer (FRET) from a host or matrix to the emitter according to the invention is particularly preferred because it is particularly efficient, leading to electronic devices with particularly good performance data (e.g., efficiency, voltage, and lifetime).It turns out that the energy transfer from a host or a matrix to the compounds according to the invention occurs preferably via Förster transfer.

[0139] These advantages mentioned above are not accompanied by an excessive deterioration of the other electronic properties.

[0140] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in the present invention may, unless explicitly excluded, be replaced by alternative features serving the same, equivalent, or similar purpose. Thus, unless otherwise stated, any feature disclosed in the present invention is to be considered an example of a generic series or an equivalent or similar feature.

[0141] All features of the present invention may be combined with each other in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations may be used separately (and not in combination).

[0142] It should further be noted that many of the features, and particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be considered merely part of the embodiments of the present invention. Independent protection may be sought for these features in addition to or alternatively to any presently claimed invention.

[0143] The teaching of technical action disclosed in the present invention can be abstracted and combined with other examples.

[0144] The invention is further illustrated by the following examples, without intending to limit it. From these descriptions, one skilled in the art can practice the invention within the entire disclosed scope and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the method according to the invention. Examples:

[0145] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are also handled in the absence of light or under yellow light. The solvents and reagents can be obtained from Sigma-ALDRICH or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds. For compounds that can exhibit multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. Synthons known from literature:

[0146] 7364-25-2 7364-26-3 1599546-91-4 LS1 LS2 LS3 1600148-88-6 1389287-44-8 51033-99-9 LS4 LS5 LS6 82722-03-0 33149-32-5 958336-66-8 LS7 LS8 LS9 2184305-49-3 2361644-30-4 2253683-27-9 LS10 LS11 LS12 97853-71-9 LS13 Synthesis of synthons S: Example B1:

[0147] Level A):

[0148]

[0149] Synthesis analogous to V. Bodmer-Narkevitch et al., Bioorg. Med. Chem. Lett. 2010, (20) 7011. A mixture of 37.1 g (100 mmol) 3-iodo-phenyl-diphenylamine [1287245-66-2], 14.8 g (110 mmol) indazolinone, LS1 [7364-25-2], 68.2 g (220 mmol) tripotassium phosphate, 952 mg (5 mmol) copper iodide, 1.14 g (10 mmol) rac-trans-1,2-diaminocyclohexane [1121-22-8], 100 g glass beads (3 mm diameter) and 500 ml dioxane is heated under reflux for 24 h. While still hot, the mixture is filtered with suction through a bed of Celite pre-slurried with dioxane, the filtrate is concentrated in vacuo, the residue is taken up in 500 ml of dichloromethane (DCM), washed three times with 200 ml of 5% aqueous EDTA solution and once with 300 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent is removed by filtration through a bed of silica gel pre-slurried with DCM, and the filtrate is slowly concentrated in vacuo, continuously replacing the distilled DCM with 100 ml of methanol.The crystallized product is filtered off with suction, washed twice with 50 ml of methanol each time, and dried in vacuo. Purification is carried out by flash chromatography (CombiFlash Torrent column system from A. Semrau, silica gel, cyclohexane / ethyl acetate (EE)). Yield: 20.5 g (54 mmol), 54%; Purity: approximately 98% by 1< H NMR. Level B): B1

[0150] 31.3 ml (50 mmol) of n-BuLi (1.6 M in n-hexane) is added dropwise to a well-stirred suspension of 18.9 g (50 mmol) of B1 (step A) in 300 ml of toluene, cooled to -78 °C. The mixture is stirred for 30 min, then allowed to warm to 0 °C over the course of 30 min, stirred for another 30 min, and cooled again to -78 °C. 50 ml (50 mmol) of boron trichloride 1 N in n-heptane is added dropwise with very thorough stirring, allowed to warm to room temperature, stirred for 1 h, and the solvent is removed in vacuo. The residue is taken up in 300 ml of o-dichlorobenzene, 18.7 ml (110 mmol) of 2,2,6,6-tetramethylpiperidine and 40.0 g (300 mmol) of anhydrous aluminum trichloride are added, and the mixture is stirred at 150 °C for 20 h. After cooling, a mixture of 29.6 ml (300 mmol) of 1,4-diazabicyclo[2.2.2.]octane and 100 ml of o-dichlorobenzene is added dropwise, the mixture is stirred for 1 h, and the mixture is filtered through a bed of Celite pre-slurried with o-dichlorobenzene, washed with o-dichlorobenzene, and the filtrate is evaporated to dryness.Further purification is carried out by continuous hot extraction (common organic solvents or their combination, preferably acetonitrile / DCM 3:1 to 1:3) or by flash chromatography (CombiFlash Torrent column system from A. Semrau, silica gel, RP silica gels, aluminum oxide, eluent: toluene / n-heptane / triethylamine, acetonitrile / THF, or DCM) and subsequent fractional sublimation or annealing under high vacuum (typically T approx. 200-400 °C, p approx. 10 -5 < to 10 -6 < mbar). Yield: 3.2 g (8.3 mmol), 16.6%; Purity: approx. 99.9% by 1< H NMR.

[0151] The following connections can be represented analogously: Example reactant product yield B2 1287245-66-2 20 % LS12 B3 1801609-87-9 18 % LS5 B4 1825341-72-7 21 % LS3 B5 1306616-39-6 16 % LS2 B6 1306616-38-5 17 % LS7 B7 1357572-67-8 15 % LS4 B8 1686100-23-1 19 % LS11 B9 1705586-11-7 15 % LS9 B10 1689530-24-2 14 % LS8 B11 1689530-26-4 16 % LS5 B12 2598066-40-9 20 % LS3 B13 1644466-58-9 19 % LS5 B14 1537218-86-2 22 % LS5 B15 2252311-13-8 17 % LS3 B16 1613370-82-3 17 % LS5 B17 834600-31-5 19 % LS12 B18 2088740-35-4 LS13 B19 1320278-50-9 16 % LS3 B20 1801610-95-6 18 % LS5 B21 2396477-58-8 20 % LS3 B22 2558183-01-8 12 % LS3 B23 2086293-14-1 21 % LS5 B24 2639695-70-6 14 % LS3 B25 185112-62-2 19 % LS5 B26 1353573-69-9 11 % LS3 B27 2152624-01-4 18 % LS3 B28 750573-24-1 18 % LS3 B29 1699755-95-7 17 % LS5 B30 1313412-22-4 24 % LS3 B31 2134579-54-5 16 % LS3 B32 345924-30-3 13 % LS5 B33 2408582-90-9 15 % LS12 B34 2098479-76-4 20 % LS5 B35 6876-00-2 16 % LS7 B36 2053644-32-7 18 % LS5 B37 2440166-44-7 17 % LS3 B38 2440166-46-9 17 % LS3 B39 1894186-07-2 21% LS5 B40 2242423-27-2 16 % LS5 B41 1579852-37-1 13 % LS3 B42 52089-10-8 9% LS6 B43 2648147-34-4 13 % LS6 B44 1257251-75-4 15 % LS6 B45 2416771-53-2 12 % LS5 B46 2416771-62-3 17 % LS5 B47 1609484-24-3 14 % LS6 B48 50 mmol in Stufe A) 25 % LS3 Use of 25 mmol Level A) to Level B) B49 1680203-50-2 20 % 50 mmol in stage A) LS5 Use of 25 mmol Level A) to Level B) B50 2059982-89-5 19 % 50 mmol in stage A) LS3 Use of 25 mmol Level A) to Level B) B51 750573-26-3 24 % 50 mmol in stage A) LS10 Use of 25 mmol Level A) to Level B) Example B100:

[0152] Level A):

[0153]

[0154] Preparation analogous to KJ Wicht et al., J. Med. Chem. 2016, 59, 6512. A well-stirred solution of 1.85 g (10 mmol) of 3-phenoxyaniline [3586-12-7] in a mixture of 50 ml of DCM and 10 ml of pyridine, cooled to 0 °C, is treated dropwise with a solution of 1.86 g (10 mmol) of 2-nitrobenzoic acid chloride [610-14-0] in 50 ml of DCM. The reaction mixture is allowed to warm to room temperature and stirred until complete conversion (approx. 6 h). The reaction mixture is poured into 200 ml of ice-water, the organic phase is separated, washed twice with 100 ml of water each time, once with 100 ml of saturated sodium chloride solution, and dried over sodium sulfate. The mixture is filtered starting with the drying agent, the filtrate is concentrated in vacuo, and the residue is stirred with 30 ml of hot methanol. Yield: 3.0 g (9.0 mmol), 90%; Purity: approximately 97% by 1< H NMR. Level B): B100

[0155]

[0156] Procedure analogous to Y. Bao et al., Org. Lett. 2020, 22, 6277. A well-stirred mixture of 3.34 g (10 mmol) of 2-nitro-N-(3-phenoxyphenyl)benzamide [1286040-75-2] (step A), 4.48 g (50 mmol) of tetrahydroxydiboron [13675-18-8], and 150 ml of methanol, cooled to 0 °C, is treated dropwise with a solution of 2.40 g (100 mmol) of NaOH in a mixture of 140 ml of methanol and 10 ml of water. The mixture is stirred for 30 min at 0 °C, then allowed to warm to room temperature and stirred for 16 h at 40 °C. Then, 200 ml of 0.5 N aqueous acetic acid is added dropwise, and the mixture is concentrated in vacuo to approximately 100 ml. The precipitated product is filtered off with suction, washed three times with 30 ml of water each time, dried twice azeotropically with 100 ml of toluene each time, and toluene residues are removed by drying in vacuo. Yield: 2.54 g (8.4 mmol), 84%; Purity: approximately 98% by 1< H NMR. C) B100

[0157] Procedure analogous to Example B1 (Step B). Batch: 3.02 g (10 mmol) (Step B). Yield: 440 mg (1.41 mmol), 14%; Purity: approx. 99.9% by 1< H-NMR.

[0158] The following connections can be represented analogously: e.g. reactant product yield B101 1030588-95-4 from level B) 19 % B102 129951-46-8 15 % 887580-43-0 B103 610-14-0 10 % 625107-12-2 B104 832151-90-3 18 % 116724-06-2 B105 832151-90-3 17 % 2222100-10-7 B106 99847-46-8 15 % 58737-02-3 B107 99847-46-8 21 % 2459228-95-4 B108 832151-90-3 11 % 3985-12-4 B109 99847-46-8 12 % 58736-39-3 B110 99847-46-8 10 % 1786434-59-0 B111 99847-46-8 8 % 114999-33-6 B112 610-14-0 12 % 866362-01-8 5 mmol in Stufe A) Use of 5 mmol of stage A) in stage B) Example: Production of OLEDs 1) Vacuum-processed devices:

[0159] The production of OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general process according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).

[0160] The following examples present the results of various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran cleaner) coated with 50 nm thick structured ITO (indium tin oxide) are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). Within 30 minutes, they are coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate), purchased as CLEVIOS™< P VP AI 4083 from Heraeus Precious Metals GmbH, Germany, spin-coated from aqueous solution) for improved processing. They are then baked at 180 °C for 10 minutes. These coated glass plates form the substrates onto which the OLEDs are applied. 1a) Blue and Green Fluorescence OLED Devices - BF and GF:

[0161] All materials are thermally evaporated in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emissive dopant (emitter) B, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:B (97:3%) means that the SMB material is present in the layer at a volume fraction of 97% and the dopant B at a volume fraction of 3%. Similarly, the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to manufacture the OLEDs are shown in Table 5.

[0162] The OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance (IUL) curves assuming a Lambertian radiation pattern, as well as the lifetime. The electroluminescence spectra are determined at a luminance of <1000 cd / m², and the color and full width half maximum (FWHM) are determined from these values. The OLEDs have the following layer structure: Substrat

[0163] Hole injection layer 1 (HIL1) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm. Hole transport layer 1 (HTL1) made of HTM1, 140 nm. Hole transport layer 2 (HTL2) made of HTM2, 10 nm. Emission layer (EML), see Table 1. Electron transport layer (ETL2), see Table 1. Electron transport layer (ETL1), see Table 1. Electron injection layer (EIL) made of ETM2, 1 nm. Cathode made of aluminum, 100 nm. Table 1: Structure of blue and green fluorescent OLED components e.g. EML ETL2 ETL1 BF1 SMB1:B3 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF2 SMB2:B5 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF3 SMB3:B8 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF4 SMB1:B14 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF5 SMB1:B16 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF6 SMB1:B23 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF7 SMB1:B24 (97:3%) 20 nm ETM1 5 nm ETM1:ETM2 (50:50%) 30 nm BF8 SMB1:B26 (97:3%) 20 nm ETM1 5 nm ETM1:ETM2 (50:50%) 30 nm BF9 SMB1:B28 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF10 SMB1:B33 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF11 SMB1:B35 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF12 SMB1:B45 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF13 SMB1:B48 (95:5%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF14 SMB1:B51 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm BF15 SMB1:B107 (97:3%) 20 nm --- ETM1:ETM2 (60:40%) 30 nm GF1 SMB1:B7 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm GF2 SMB1:B12 (97:3%) 20 nm --- ETM1:ETM2 (50:50%) 30 nm Table 2: Results of blue (420-499 nm) and green (500-540 nm) fluorescent OLED devices e.g. EQE [%] 1000 cd / m 2 Voltage [V] 1000 cd / m 2< Color FWHM [eV] BF1 8.8 3.7 blue 0.20 BF2 7.9 3.6 blue 0.16 BF3 7.7 3.5 blue 0.17 BF4 7.2 3.7 blue 0.22 BF5 8.5 3.5 blue 0.18 BF6 8.3 3.7 blue 0.16 BF7 8.8 3.5 blue 0.16 BF8 8.6 3.5 blue 0.15 BF9 9.1 3.8 blue 0.16 BF10 7.9 3.6 blue 0.18 BF11 8.4 3.8 blue 0.16 BF12 8.1 3.6 blue 0.17 BF13 8.8 3.8 blue 0.21 BF14 9.4 3.6 blue 0.19 BF15 7.0 3.7 blue 0.24 GF1 9.1 3.3 green 0.23 GF2 10.3 3.3 green 0.20 1 b) Hyperphosphorescent OLED components:

[0164] All materials are thermally evaporated in a vacuum chamber. The emission layer (EML) or layers always consist of at least one matrix material (host material) TMM, a (phosphorescent) sensitizer PS, and a fluorescent emitter B. The sensitizer PS and fluorescent emitter B are mixed into the host material TMM by co-evaporation in a specific volume fraction. A specification such as TMM:PS(8%):B(1%) means that the TMM material is present in the layer at a volume fraction of 91%, PS at 8%, and fluorescent emitter B at 1%. Blue hyperphosphorescent OLED devices BH:

[0165] The OLEDs basically have the following layer structure: Substrate: Hole injection layer 1 (HIL1) made of HTM2 doped with 5% NDP-9 (commercially available from Novaled), 20 nm hole transport layer 1 (HTL1) made of HTM2, 30 nm hole transport layer 2 (HTL2), see Table 3. Emission layer (EML), see Table 3. Electron transport layer (ETL2), see Table 3. Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 20 nm electron injection layer (EIL) made of ETM2, 1 nm cathode made of aluminum, 100 nm Table 3: Structure of blue hyperphosphorescent OLED components e.g. HTL2 EML ETL2 BH1 HTM3 10 nm TMM1:PS1(8%):B21(1%) 25 nm ETM3 10 nm BH2 HTM3 10 nm TMM1:PS1(8%):B34(1%) 25 nm ETM3 10 nm Table 4: Results e.g. EQE (%) 100 cd / m 2 Voltage (V) 100 cd / m 2< Color EL-FWHM [eV] BH1 15.9 3.6 Blue 0.23 BH2 17.0 3.7 Blue 0.19 Table 5: Structural formulas of the materials used HTM1 HTM2 136463-07-5 1450933-44-4 HTM3 TMM1 = ETM3 1206465-62-4 1201800-83-0 SMB1 SMB2 [1087346-88-0] [667940-34-3] SMB3 PS1 [1627916-48-6] 1541114-98-0 ETM1 ETM2 25387-93-3 1233200-52-6

[0166] The abbreviations shown in Tables 1 and 3 with respect to the materials according to the invention, such as B3, B5, B7, B8, B12, B14, B16, B21, B34, B23, B24, B26, B28, B33, B35, B45, B48, B51 and B107 etc., refer to the compounds detailed in the synthesis examples above.

[0167] The compounds according to the invention show narrow electroluminescence spectra, recognizable by the lower EL-FWHM values ​​( EL electroluminescence - F ull W idth H alf M aximum - width of the EL emission spectra in eV at half peak height). Narrow electroluminescence spectra lead to significantly improved color purity (smaller CIE y values). In addition, very good EQE values ​​( E external Q uantes E efficiencies) at low operating voltages, which leads to significantly improved performance efficiencies of the device and thus to lower power consumption.

Claims

1. Compound comprising at least one structure of the formula (I), where the further symbols used are as follows: Za, Zb is the same or different at each instance and is N, CR, or the Za, Zb groups form a ring Ara, where the ring Ara is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R2 radicals, where the ring Ara together with the CO group and the Wa, Wb groups forms a 5-membered ring; Wa, Wb is the same or different at each instance and is NR, NAr, NB(R)2 or NB(Ar)2, where exactly one of the Wa, Wb groups is NB(R)2, NB(Ar)2, and exactly one of the Wa, Wb groups is NR, NAr, or the Wa, Wb groups form a ring of the formula where Z° is R or Ar, the ring Arb is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Rb radicals, where the ring Arb may form a ring system with an R, Ar or Z° group or the rings Ara and Arb together may form a ring system, and the dotted lines represent the bonds to the CO group or Zb group; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, R, Ra, Rb group or a further group; R, Ra, Rb is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R')2, C(=O)N(Ar')2, C(=O)N(R1)2, C(Ar')3, C(R1)3, Si(Ar')3, Si(R1)3, B(Ar')2, B(R1)2, C(=O)Ar', C(=O)R1, P(=O)(Ar')2, P(=O)(R1)2, P(Ar')2, P(R1)2, S(=O)Ar', S(=O)R1, S(=O)2Ar', S(=O)2R1, OSO2Ar', OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C=CR1, C=C, Si(R1)2, C=O, C=S, C=Se, C=NR1, -C(=O)O-, -C(=O)NR1-, NR1, P(=O)(R1), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals; or heteroarylthio group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or a diarylamino, arylheteroarylamino, diheteroarylamino group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or an aralkyl or heteroarylalkyl group which has 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl radical and may be substituted by one or more R1 radicals; at the same time, two R, Ra, Rb radicals together or with a further group may also form a ring system; Ar' is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals; at the same time, it is possible for two Ar' radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C=O, C=NR1, C=C(R1)2, O, S, S=O, SO2, N(R1), P(R1) and P(=O)R1; R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R2 )2, C(=O)Ar", C(=O)R2, P(=O)(Ar")2, P(Ar")2, B(Ar")2, B(R2)2, C(Ar'')3, C(R2)3, Si(Ar'')3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by -R2C=CR2-, -C≡C-, Si(R2)2, C=O, C=S, C=Se, C=NR2, -C(=O)O-, -C(=O)NR2-, NR2, P(=O)(R2), -O-, -S-, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems; at the same time, two or more R1 radicals together may form a ring system; at the same time, one or more R1 radicals may form a ring system with a further part of the compound; Ar'' is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R2 radicals; at the same time, it is possible for two Ar'' radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C=O, C=NR2, C=C(R2)2, O, S, S=O, SO2, N(R2), P(R2) and P(=O)R2; R2 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R2 together may form a ring system.

2. Compound according to Claim 1, characterized in that the Wa, Wb groups form a ring of the formula where the symbols Arb and Zc have the definition given above.

3. Compound according to Claim 1 or 2, comprising at least one structure of the formula (II-1) to (II-18), where the symbols R, Ar, Ara and Arb have the definitions given in Claim 1 and X is the same or different at each instance and is N or CR.

4. Compound according to one or more of Claims 1 to 3, comprising at least one structure of the formulae (III-1) to (III-48), where the symbols Ar and R have the definitions given in Claim 1 and the further symbols are as follows: X is the same or different at each instance and is N or CR, with the proviso that not more than two of the X groups in one cycle are N, where R has the definition detailed in Claim 1; Xa is the same or different at each instance and is N or CRa, with the proviso that not more than two of the Xa groups in one cycle are N, where Ra has the definition detailed in Claim 1; Xb is the same or different at each instance and is N or CRb, with the proviso that not more than two of the Xb groups in one cycle are N, where Rb has the definition detailed in Claim 1, Y1 is the same or different at each instance and is a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I); Y2 is the same or different at each instance and is a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al (Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I); Y3 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al (Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I); Y4 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, C(R)2, Si(R)2, O or S, where R has the definition detailed above, especially for formula (I); Y5 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I); Y6 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al (Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I).

5. Compound according to one or more of Claims 1 to 4, comprising at least one structure of the formulae (IV-1) to (IV-48), where the symbols R, Ra and Rb have the definitions given in Claim 1, the symbols Y1, Y2, Y3, Y4, Y5 and Y6 have the definitions given in Claim 3, and the further symbols are as follows: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2; k is 0 or 1.

6. Compound according to one or more of Claims 1 to 5, characterized in that the structures / compounds of the formulae (I), (II-1) to (II-18), (III-1) to (III-48) and / or (IV-1) to (IV-48) have not more than one olefinic double bond.

7. Compound according to one or more of Claims 1 to 6, characterized in that at least two R, Ra, Rb radicals together with the further groups to which the two R, Ra, Rb radicals bind form a fused ring, where the two R, Ra, Rb radicals form at least one structure of the formulae (RA-1) to (RA-12) where R1 has the definition set out above, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R, Ra, Rb radicals bind, and the further symbols are defined as follows: Y7 is the same or different at each instance and is C(R1)2, (R1)2C-C(R1)2, (R1)C=C(R1), NR1, NAr', O or S; Rc is the same or different at each instance and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, C=O, C=S, C=Se, C=NR2, -C (=0) 0-, -C(=O)NR2-, NR2, P(=O)(R1), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals; at the same time, it is also possible for two Rc radicals together or one Rc radical together with an R1 radical or together with a further group to form a ring system; s is 0, 1, 2, 3, 4, 5 or 6; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

8. Compound according to one or more of Claims 1 to 7, characterized in that at least two R, Ra, Rb radicals together with the further groups to which the two R, Ra, Rb radicals bind form a fused ring, where the two R, Ra, Rb radicals form structures of the formula (RB), where R1 has the definition detailed in Claim 1, the dotted bonds represent the sites of attachment via which the two R, Ra, Rb, Rc, Rd radicals bind to the further groups, the index m is 0, 1, 2, 3 or 4 and Y8 is C(R1)2, NR1, NAr', BR1, BAr', O or S.

9. Compound according to one or more of Claims 1 to 8, comprising at least one structure of the formulae (V-1) to (V-12), where the compounds have at least one fused ring, where the symbols Ra, Rb, Y1, Y2 and Y5 have the definitions given in Claim 1 or Claim 3, the symbol o represents the sites of attachment, and the further symbols have the following definition: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1, or 2.

10. Compound according to one or more of Claims 1 to 9, characterized in that at least one substituent R, Ra, Rb is the same or different at each instance and is selected from the group consisting of H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulae Ar-1 to Ar-78, where R1 has the definitions given above, the dotted bond represents the bond to the corresponding group and in addition: Ar1 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R1 radicals; A is the same or different at each instance and is C(R1)2, NR1, O or S; p is 0 or 1, where p = 0 means that the Ar1 group is absent and that the corresponding aromatic or heteroaromatic group is bonded directly to the corresponding radical; q is 0 or 1, where q = 0 means that no A group is bonded at this position and R1 radicals are bonded to the corresponding carbon atoms instead.

11. Compound according to at least one of the preceding Claims 1 to 10, characterized in that the compound comprises exactly two or exactly three structures of formula (I), (II-1) to (II-18), (III-1) to (III-48), (IV-1) to (IV-48) and / or (V-1) to (V-12).

12. Oligomer, polymer or dendrimer containing one or more compounds according to any one of Claims 1 to 10, wherein, in place of a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

13. Formulation comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 and at least one further compound, where the further compound is preferably selected from one or more solvents.

14. Composition comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

15. Process for preparing a compound according to one or more of Claims 1 to 11, characterized in that a base skeleton having at least one of the Wa groups or a precursor of one of the Wa groups is synthesized, and an aromatic or heteroaromatic radical is introduced by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

16. Use of a compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 in an electronic device.

17. Electronic device comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12.